Dicarboxylic acid bis(3,5-dicarbamoyl-2,4,6-triiodoanilides) useful as x-ray contrast agents

Abstract

Dicarboxylic acid bis(3,5-dicarbamoyl-2,4,6-triiodoanilides) of the formula <IMAGE> wherein R1 is lower straight-chain or branched-chain mono- or polyhydroxyalkyl; R2 is hydrogen, lower alkyl or R1; R3 is hydrogen or lower alkyl; and X is a direct bond or straight-chain or branched-chain alkylene interrupted by one or more oxygen or substituted by hydroxy or lower alkyl, are useful in x-ray contrast media.

What is claimed is: 
     
       1. A compound of the formula ##STR7## wherein R 1  is alkyl of 2-8 carbon atoms substituted by 1-5 hydroxyl on separate carbon atoms thereof, other than the α-carbon atom; R 2  is hydrogen, alkyl of up to 4 carbon atoms or R 1  ;   R 3  is hydrogen or alkyl of 1-4 carbon atoms;   X is a direct bond or straight-chain or branched-chain alkylene, oxaalkylene, dioxaalkylene, or trioxaalkylene of up to 6 carbon atoms, wherein the oxygen atoms of the di- and trioxaalkylenes are separated from each other and from the ends thereof by at least one methylene.   
     
     
       2. Oxalic acid bis[3,5-bis(2,3-dihydroxypropyl-N-methylcarbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       3. Oxalic acid bis[3,5-bis(2-hydroxyethylcarbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       4. Oxalic acid bis[3,5-bis(2-hydroxyethyl-N-methylcarbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       5. Oxalic acid bis[3,5-bis(N,N-bis[2-hydroxyethyl}carbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       6. Oxalic acid bis[3,5-bis(3-hydroxypropylcarbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       7. Oxalic acid bis[3,5-bis(2-hydroxypropylcarbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       8. Oxaglutaric acid bis[3,5-bis(2,3-dihydroxypropyl-N-methylcarbamoyl)-2,4,6-triiodo-N-methylanilide], a compound of claim 1. 
     
     
       9. Malonic acid bis[3,5-bis(2,3-dihydroxypropyl-N-methylcarbamoyl)-2,4,6-triiodo-N-methylanilide], a compound of claim 1. 
     
     
       10. Adipic acid bis[3,5-bis(2,3-dihydroxypropyl-N-methylcarbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       11. Adipic acid bis[3,5-bis(1,3-dihydroxyisopropylcarbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       12. 3,6-Dioxasuberic acid bis[3,5-bis(2,3-dihydroxypropyl-N-methylcarbamoyl)-2,4,6-triiodoanilide], a compound of claim 1. 
     
     
       13. A compound of the formula ##STR8## wherein R 3  is H or alkyl and X is a direct bond or straight-chain or branched-chain alkylene oxaalkylene, dioxaalkylene, or trioxaalkylene of up to 6 carbon atoms, wherein the oxygen atoms on the di- and trioxaalkylenes are separated from each other and from the ends thereof by at least one methylene. 
     
     
       14. Oxalic acid bis[3,5-bis(chlorocarbonyl)-2,4,6-triiodoanilide], a compound of claim 13. 
     
     
       15. Oxaglutaric acid bis[3,5-bis(chlorocarbonyl)-2,4,6-triiodo-N-methylanilide], a compound of claim 13. 
     
     
       16. Malonic acid bis[3,5-bis(chlorocarbonyl)-2,4,6-triiodo-N-methylanilide], a compound of claim 13. 
     
     
       17. Adipic acid bis[3,5-bis(chlorocarbonyl)-2,4,6-triiodoanilide], a compound of claim 13. 
     
     
       18. 3,6-Dioxasuberic acid bis[3,5-bis(chlorocarbonyl)-2,4,6-triiodoanilide], a compound of claim 13. 
     
     
       19. An x-ray contrast agent adapted for oral or intravenous administration comprising a radiopaque amount per unit dosage of a compound of claim 1, in admixture with a pharmaceutically acceptable carrier. 
     
     
       20. A method for conducting a radiological examination of a patient which comprises administering thereto prior to examination a radiopaque amount of a compound of claim 1.